Caroline in the City Guide to Sydney

This is a new feature to Caroline in the City, the city guides to my favorite destinations in the world, featuring the best places to eat, stay and hang out. 

Beyond the famous tourist attractions like the Harbour Bridge and the Opera House, Sydney is a chic, metropolis on the ocean. It’s surrounded on water by three sides, including the Parramatta River. There’s also the northern and southern beaches as well as the western suburbs.

It’s easily accessible by public transportation, with trains, buses and ferries servicing the area. Most people who visit stay within the confines of the CBD, but if you venture out further, you’ll be surprised at what you might find, from the cultural enclaves like Italian Leichardt to the hipster cafes in Newtown and Erskineville.

The Neighborhoods of Sydney

Sydney is a fairly large city, so each neighborhood feels like its own little town. I lived in Marrickville, in the Inner West, so most of my knowledge about Sydney neighborhoods is limited to that part of town. Each has their own beloved bars, restaurants, cafes and shops.

Newtown is where I spent most of my time, a quirky suburb popular with students for its street art and cafes. It was a short bus ride from where I lived and chock full of places to eat, lining King Street. I usually started off my day at a cafe like VargaBar Espresso before relaxing in Camperdown Memorial Rest Park to admire its ever changing street art.

I spent hours wandering the shops, including Gould’s Books, T2 Tea and the Vinnie’s thrift store. When I got sick of the slow WiFi at my apartment, I headed over to the Newtown Library to use theirs for free. The Dendy Newtown is a popular spot for arthouse movies.

Nearby Erskineville, located between Newtown and Alexandria, is smaller in size than its neighboring suburbs, but has a surprising number of businesses to make up for it. It’s within walking distance of three train stations, so I stopped here a few times to wander around before hopping back on the train. 

Cafe Shenkin was one of my favorite spots here, as it has open windows for people watching and features a Mediterranean menu. The Imperial Hotel is one of the city’s most prolific gay nightlife spots. Erskineville also has its own park and sports oval.

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I didn’t do much exploring in Alexandria, but I’ve heard so much about the area since I left. Friends have told me about The Grounds of Alexandria, a hip coffee shop and restaurant popular with locals. The neighborhood also encompasses the sprawling Sydney Park, a great place to spend an afternoon in the sun.

Surry Hills and Darlinghurst are both on the border with King’s Cross, but have surprising places on side streets you might not find on your own. Shady Pines Saloon is a speakeasy of sorts that reminds me of an American hunting lodge.

When I first arrived, I wanted to live in Glebe, which is within walking distance of the city centre and has weekly markets and dozens of fantastic restaurants. Starting at the Broadway shopping center, Glebe Point Road runs through the neighborhood. Some of my favorite Glebe hangouts were Gleebooks, Badde Manors and, of course, the Glebe Markets.

The beach suburbs were highly sought after and I was lucky to have friends who lived in them. Manly to the north is accessible by ferry and has lots of up-and-coming restaurants. There’s also a pedestrian shopping street with your favorite chain stores. It feels a lot like Los Angeles’ Venice Beach.

Across the bay is the famous Bondi, where the city’s young and beautiful live and play. I preferred the more laid back beach suburb of Coogee, where my friends and I would have Sunday sessions.

Sydney Restaurants and Cafes

The common theme of my year in Australia is doing things on the cheap, so most of my favorite restaurants cost under $20 for a meal and drink. They feature both classic Australian fare and the ethnic eateries that make Sydney such a great place to live.

The Australian Heritage Hotel is where I would always take visitors to Sydney because it’s such a classically old school Sydney pub. They serve craft Aussie brews and deluxe pizza with toppings like kangaroo and crocodile.

Chat Thai is one of a handful of restaurants anywhere that I’ll stand in line for hours for. As you’re lined up in front of the restaurant, you can see the cooks creating classic Thai dishes through the window. It creates your appetite so that when you and your friends get inside, you can order a nice assortment to share.

Harry’s Cafe De Wheels is a Sydney icon and the city’s first “food truck.” Today it’s busy at all hours and has multiple locations, each serving up their classic meat pies, topped with mash, gravy and peas.

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Big Brekky was the first place I ate in Sydney. The Petersham cafe is known for, you guessed it, their breakfasts, like massive omelets and fruit plates. It’s on a quieter stretch of street, so you’ll find only locals here.

Flying Fajita Sistas is one of the only approved Mexican restaurants I visited in Sydney. There are a number of Tex-Mex style, but this was the only place I found tamales as well as a full selection of Mexican beers and hot sauces.

Guzman y Gomez Mexican Taqueria Newtown was my go-to for a quick burrito fix. They had a Tabasco bar and served frozen margaritas, Mexican beers and even Mexican sodas. Plus, you got a free burrito after you bought 10. I may have gone through two customer cards…

For more on the best cafes in Sydney, check out my friend Jayne’s post on Sydney’s Coolest Cafes and Coffee Shops. 

Sydney Bars and Nightlife

I worked in a bar for most of my time in Australia, so I didn’t go out as much as some people do. And when I did, it wasn’t until my bar closed at midnight, limiting my options to a few around Circular Quay and the many nightspots of King’s Cross that stay open until the wee hours. My favorite bars were laid back spots where I could have a casual beer or that I could hang out all night.

The Glenmore Hotel has arguably the best view of the harbor. Head to the roof for the full experience.

Harts Pub was a place I only discovered in my last week, but wish I’d been more. They are the home to the Rocks Brewing Company and have a full menu of upscale bar food.

Opera Bar is an icon in the city, located beneath the Opera House.

Scubar is one of the best backpacker bars anywhere, located below the Central YHA. They host weekly crab racing and contests for travelers, as well as happy hour on jugs of beer and cocktails.

Shady Pines Saloon is, as I mentioned earlier, a hipster speakeasy that looks like nothing from the outside. Once inside, you see mustachioed bartenders ready to serve you classic cocktails.

Things to Do in Sydney

Sydney’s tourist attractions run the gamut from must-see to expensive and overrated. But here are a few things to do that I recommend, including a handful that are free and will keep your costs low.

Museum of Contemporary Art is right in the tourist hub of Circular Quay but the galleries of modern art feel worlds away. It’s free to visit, apart from the special exhibits, and the patio of their cafe offers the best views of the harbor.

Bondi to Bronte Walk actually extends all the way to Coogee, cutting through the cliffside neighborhoods and five beaches. It runs 5 kilometers and involves a lot of stairs, but is free exercise. Last time I spotted Gerard Butler there!

The Sydney Opera House is the ultimate icon in the city, but if you don’t have time to catch a show, be sure to go on the behind the scenes tour to see the architecture up close.

BridgeClimb is a more pricey attraction, but you can’t beat the experience. You’re placed in a special suit and clipped onto the railings. Once you reach the top, you get sweeping views of the city and harbor.

Free Walking Tour leaves daily from Sydney Town Hall and provides information on the city’s history. They also have a nightly tour in The Rocks.

Cockatoo Island is a national park on a former convict island that has been transformed to a campsite that holds special events like art exhibits and pop-up restaurants.

Urban Adventures runs a number of tours in the city covering different aspects of Sydney’s history, from the early days of The Rocks to the most infamous tales from Kings Cross.

Shopping in Sydney

What makes Sydney a great city for shopping is its neighborhood markets, each offering different expertise. The Rocks Market is one of the most popular, held weekly in the city’s oldest neighborhood. Here you’ll find both souvenirs and handmade goods. Glebe Markets include more secondhand clothing and jewelry vendors while Reverse Garbage in Marrickville feels more like a flea market. There are also weekly markets in Bondi, Rozelle, Paddington and Surry Hills.

For more on Sydney’s markets, read this post on Time Out Sydney.

Where to Stay in Sydney

It’s an expensive place to stay, but once you get outside of the tourist areas like Circular Quay and Darling Harbour, you can experience more of the local’s side of Sydney.

Sydney Central YHA is well located in town, right across from the free bus stop and the main train station. You can choose from both dorms and private rooms. The hostel has a kitchen, rooftop pool and movie theater.

There are other locations further out from the city, including the Glebe Point YHA and Bondi Beachouse YHA. Another option is Tara, a guesthouse in the Inner West suburb of Enmore.

Transportation in Sydney

Considering its size, Sydney is a highly walkable city. I would regularly walk from Central Station to Circular Quay without thinking much of it. There’s a free bus that runs the same distance. Trains, trams, buses and ferries operate in the city to get you around, but most stop running or run less frequently after midnight.

Grab an Opal card if you’ll be taking multiple forms of transport during your stay. The train runs directly from the airport into the city center.

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Have you been to Sydney, Australia? Share your tips below!